Laboratoire de Glycochimie, des Antimicrobiens
et des Agroressources UMR 7378 CNRS

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Actualités et Publications

Prix de thèse 15ème édition - 2018

Félicitation à Mehdi OMRI


Metal-free oxidative esterification of benzylated monosaccharides,

Camara, T.; Bil, A.; Chagnault, V.

Carbohydr. Res. 2018.

Methyl glyconates have been attracting considerable attention as intermediates for the preparation of aryl C-glycosides, polyphenolic products, aliphatic polyesters, SGLT2 inhibitors, antibiotics etc … In view of the interest in those compounds, we report herein our work on the synthesis of methyl glyconates using an oxidative esterification carried out by molecular iodine. This reaction is catalyzed by non-toxic K4Fe(CN)6 that releases a small amount of cyanide ion into the reaction mixture. Four benzylated carbohydrates which contain a hemiacetalic functional group have been tested successfully.

Water-mediated synthesis of disubstituted 5-aminopyrimidines from vinyl azides under microwave irradiation,

Dehbi, O.; Ishak, E. A.; Bakht, M. A.; Geesi, M. H.; Alshammari, M. B.; Chagnault, V.; Kaiba, A.; Lazar, S.; Riadi, Y.

Green Chemistry Letters and Reviews 2018, 11, 62-66.

An efficient and ecofriendly method for the synthesis of disubstituted 5-aminopyrimidines from vinyl azides and urea or thiourea was developed. This reaction proceeds under microwave irradiation conditions in the presence of water as a solvent. The remarkable features of this new protocol are high conversion, short reaction times, cleaner reaction profiles and straightforward procedure.

New iodide-based amino acid molecules for more sustainable electrolytes in dye-sensitized solar cells,

Sagaidak, I.; Huertas, G.; NguyenVan Nhien, a.; Sauvage, F.

Green Chem. 2018.

The electrolyte is the second key component governing at once power conversion performances and stability of dye-sensitized solar cells. Towards the integration of more sustainable materials, we focused in the replacement of the major constituent of the electrolyte, namely the 1,3 di-alkyl imidazolium iodide. We synthesized two new iodide molecules derived from natural amino acid family (L-proline): (S)-2-(methoxycarbonyl)-1,1-dimethylpyrrolidinium iodide (PMeI) and (S)-2-(ethoxycarbonyl)-1,1-ethylpyrrolidinium iodide (PEtI). In combination with the C106 polypyridyl ruthenium(+II) sensitizer, power conversion efficiencies of 7.1% for PMeI and 6.5% for PEtI were obtained under standard Air Mass 1.5G conditions in conjunction with low-volatile 3-methoxypropionitrile-based solvent. The relationship between these new iodide molecules, the power conversion efficiency and interfacial charge transfer processes is herein discussed and systematically compared to the best standard 1,3 di-methylimidazolium iodide.

Gold Catalysis and Photoactivation: A Fast and Selective Procedure for the Oxidation of Free Sugars,

Omri, M.; Sauvage, F.; Busby, Y.; Becuwe, M.; Pourceau, G.; Wadouachi, A.

ACS Catalysis 2018, 1635-1639.

A fast and efficient methodology for the selective oxidation of sugars into corresponding sodium aldonates is herein reported. Hydrogen peroxide was used as a cheap oxidant and electron scavenger, in the presence of only 0.003-0.006 mol % of gold in basic conditions. Three photocatalysts were studied, namely Au/Al2O3, Au/TiO2 and Au/CeO2, the latter being the most efficient (TOF > 750 000 h-1) and perfectly selective. Only 10 minutes exposition under standard incident sunlight irradiation (A.M.1.5G conditions - 100 mW/cm2) affords total conversion of glucose into the corresponding sodium gluconate. Demonstrating its versatility, this methodology was successfully applied to a variety of oligosaccharides leading to the corresponding aldonates in quantitative yield and high purity (>95%) without any purification step. The photocatalyst was recovered by simple filtration and re-used 5 times leading to the same conversion and selectivity after 10 min of illumination.

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